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Oyster Bay Hamlet Is the Heart of the Oakcliff Sailing Center’s Team Building

Harvest Regatta Kick-Off Party on Friday, October 8

Dawn Riley of the Oak Cliff Sailing Center is bringing the world to Oyster Bay – the sports world, demonstrated by their motto: “Raising the level of sailors and sailing in the U.S.”

Oakcliff Sailing Center – with its base in Oyster Bay - is a non-profit organization, whose mission is to raise the level of the sport internationally. Dawn Riley, the executive director of Oakcliff Sailing since January of 2010, said simply, “We equip people with skills.” The Sailing Center is still incorporating bits and pieces of her plan, “but it is moving forward well,” she announces, proudly.

Ms. Riley’s work entails training groups of people who have had little or no experience with sailing. Often, these lessons are requested by corporations, who are determined to have their employees work synergistically, toward a common goal.

She has done this before: coordinated these sessions by searching out and establishing a location, obtaining the equipment (including boats), and finding nightly accommodations for each group she coached. Oak Cliff Sailing Center has provided a nearly ideal situation for her trainings here in Oyster Bay, which is easily accessible to New York City. Now, groups from all over the U.S. come directly to her.

She admitted that the Center has had to rely mostly on spare rooms and couches for their guests. “Ideally, there would be a couple of quaint B&Bs in downtown Oyster Bay,” she says, quickly adding “I can assure you that our sailing supporters have assisted the bottom line of the bars and restaurants in town.”

Besides adding to the economy in the hamlet, another facet of Oakcliff Sailing Center is the Acorn Program. This program grants scholarships to potential racing sailors who are between 18 and 30 years old. Not only does the program help them to become accomplished sailors, but the skills they learn can also be used to attain important business capabilities.

It is obvious that Ms. Riley is an extremely busy woman, who runs on a tight schedule. In spite of that however, she is very composed, and possesses a commanding presence. It is easy to see why she is also widely respected as a motivational speaker. She has spoken at more than 100 events for various corporations. Her passion for sailing has influenced her from a young age. She grew up in Michigan, sailing on Lake St. Clair, and was a competitive sailor by the age of 13. She was drawn to working with big boats, as opposed to Olympic sailing, because she truly enjoys putting a team together.

She has been a competitor in the America’s Cup and the Whitbread Round the World (sailboat racing competitions). Ms. Riley has been affiliated with the Women’s Sports Foundation from 1999-2006, and was president of that foundation from 2003-2004. She also published a book, entitled Taking the Helm, which is an account of her experience leading a women’s team whose boat had undergone a mutiny. Additionally, Ms. Riley has been recognized as the Young Leader for the Herbert Quant Foundation and the Aspen Institute Programs (corporate think tanks).

Ms. Riley began her teambuilding efforts in 1989-1990, for corporations. Business really took off in 1993 and 1994, when there was an abundance of corporate take-overs. This paved the way for team-building. In regard to team building, Ms. Riley enjoys dealing with people, facilitating the teamwork and the challenge. Sailing naturally lends itself to teaching teamwork, which also can be applied to business, budgeting and accounting. “It is a good equalizer,” Dawn explains. For example, in a high school setting, you have a hierarchy of kids, functioning in their separate groups. “However, once you get them all on a boat, (assuming none of them are experienced sailors), they are suddenly equals.”

Ms. Riley points out that on a boat, you must establish leadership. Someone has to step up and others follow, “or else you’re not going anywhere,” Dawn advises. The leader must be consistent, so that the team is all moving in the same direction. In fact, consistency is more important than doing things the “right” way. “There is no right or wrong way,” Dawn says, “It’s the Oakcliff way.” To illustrate the importance of teambuilding, she uses an example; “To get around the top mark you have 16 people on a boat, and 73 things have to happen in 13 seconds.” There is little room for error. Additionally, communication and interpersonal relationships play into the ultimate success of a crew working smoothly together. Another area that is paramount in sailing is “risk and reward.” There is always calculated risk-taking in sailing. “It is about strategizing, and having a healthy respect of the sea and wind. If you don’t, it’s going to come back and bite you,” Ms. Riley advises, knowingly.

Dawn said that fall and spring are the “busy seasons” for sailing, as the wind is better, although this summer provided beautiful sailing conditions. “In the fall we tend to sail the bigger boats. We have sailing opportunities for new racers through our Harvest Regatta Oct. 8 and 9, and for experienced racers through Thanksgiving.”

The Harvest Regatta Kick-Off Party is an upcoming event intended to jump-start the fall sailing season. It will take place on Friday, Oct. 8, from 6:30 to 11 p.m. The event being held in conjunction with the Main Street Association will feature a strolling dinner, an art show and a silent auction, then, live music and dancing will take place in the boat hall. This will bring together competitive sailors, community leaders and supporters of Oakcliff Sailing Center. To purchase tickets at $75 each, Ms. Riley directs those interested to the Oakcliff Sailing Center site, at